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Palladium-ion multi-channel response probe and synthesis method and application thereof

A synthesis method and technology of palladium ions, which are applied in the direction of chemical reaction of materials, material analysis by observing the influence of chemical indicators, and material analysis by optical means, which can solve problems such as few researches.

Active Publication Date: 2017-01-11
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few studies on this kind of photoactive and electroactive sensors at the same time (Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P.J.Org.Chem. 2008, 73, 5489-5497.), especially For Pd 2+ The study of photoactive multi-channel detection probes for ions has not been reported so far

Method used

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  • Palladium-ion multi-channel response probe and synthesis method and application thereof
  • Palladium-ion multi-channel response probe and synthesis method and application thereof
  • Palladium-ion multi-channel response probe and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of Rhodamine Glide Hydrazide

[0055] In a 100mL two-necked flask equipped with a stirring magnet and a spherical condenser, add rhodamine B (1.000g, 2.10mmol), ethanol (20mL) and hydrazine hydrate (80%, 0.50mL, 8.60mmol) successively, and stir Heat under reflux until the reaction solution turns from dark red to light yellow, and the reaction temperature is 80°C, stop heating, and cool to room temperature. The solvent was distilled off under reduced pressure, and the residue was separated by column chromatography (ethyl acetate / petroleum ether=1:1, R f =0.40), 0.800 g of light pink solid was obtained, the yield was 83%, m.p.: 179-181°C.

Embodiment 2

[0057] Synthesis of Ferrocene-Rhodamine Probe

[0058] In a 50mL two-necked flask equipped with a stirring magnet and a spherical condenser, add rhodamine lactam (0.100g, 0.22mmol), ferrocene formaldehyde (0.050g, 0.22mmol), ethanol (3.0mL) and ice Acetic acid (0.01mL), the mixed solution was stirred and heated to reflux, the reaction temperature was 80°C, followed by thin layer chromatography, after the reaction was complete, the solvent was evaporated under reduced pressure, and the residue was separated by column chromatography (ethyl acetate / petroleum ether = 1:1, R f =0.30), to obtain 0.120 g of an orange powdery solid, with a yield of 85%, m.p.: 165-167° C. 1 H NMR (300MHz, CDCl 3 ,TMS):δ8.29(s,1H),8.00(d,1H,J=6.0Hz),7.49(m,2H),7.12(d,1H,J=6.0Hz),6.60(s,2H) ,6.49(d,2H,J=3.0Hz),6.30(d,2H,J=3.0Hz),4.51(s,2H),4.24(s,2H),3.86(s,5H),3.35(q, 8H, J=7.0Hz), 1.16(t, 12H, J=7.0Hz). 13 C NMR (75MHz, CDCl 3 ,TMS): δ164.27,153.06,151.72,148.95,148.68,132.94,129.62,128.13,123.64...

Embodiment 3

[0060] Ultraviolet Spectrum Detecting the Effects of Probes on Various Metal Ions

[0061] Prepare 1.25×10 in a 50mL volumetric flask -4 Probe molecule THF solution in the embodiment 2 of M, prepare 2.5 * 10 respectively in 10mL volumetric flask -2 Aqueous solutions of different metal ions of M; respectively pipette 2.0mL1.25×10 in a 10mL volumetric flask - 4 The probe molecule THF solution of M and 20 μL of the above-mentioned metal ion aqueous solution were fixed to volume with deionized water, and their ultraviolet absorption spectra were measured respectively ( figure 1 ).

[0062] The results show that only adding Pd 2+ ion, the ultraviolet spectrum absorption of the probe molecule changes significantly, and a new strong ultraviolet absorption peak appears at 560nm, indicating that the probe molecule can be highly selective with Pd 2+ Ionic coordination.

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Abstract

The invention discloses a palladium-ion multi-channel response probe and a synthesis method and application thereof. A probe molecule is formed by connecting ferrocene serving as an electric signal response center with rhodamine B serving as an optical signal response center through an acyl hydrazone bridge. The response probe is characterized in that Pd<2+> ions in an aqueous phase can be detected in a high-selectivity mode through the means of ultraviolet light or fluorescence or color comparison or electrochemistry, the lowest detection limit is 5.06*10<-8> M, and the response probe can be applied to cell fluorescence imaging. The probe is the first probe which has the photoelectric dual activity and can achieve multi-channel detection of the Pd<2+> ions, can efficiently detect a trace amount of Pd<2+> ions in different environments and is diverse in detection means, good in selectivity and wide in application prospect.

Description

technical field [0001] The invention belongs to the field of photoelectric functional materials, and in particular relates to the design, synthesis method and application of a palladium ion multiple response probe. Background technique [0002] With the rapid development of new drug development and organic synthesis methodology, palladium has been more and more widely used in these fields as the most important catalyst in platinum group metals ((1) Magano, J.; Dunetz, J.R.; Chem.Rev. 2011, 111, 2177-2250. (2) Nicolaou, K.C.; Bulger, P.G.; Sarlah, D. Angew. Chem., Int. Ed. .; Mignani, G.; Scholz, U. Adv. Synth. Catal. 2006, 348, 23-39. (4) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2310. ) Tietze, L.F.; Ila, H.; Bell, H.P. Chem. Rev. 2004, 104, 3453-3516. (6) Lyons, T.W.; Sanford, M.S. Chem. Rev. 2010, 110, 1147-1169.). However, because palladium has excellent coordination properties, it is easy to remain in the drug ((1) Reginato, G.; Sadler, P.; Wilkes, R.D.Org.Pr...

Claims

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Application Information

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IPC IPC(8): G01N21/33G01N21/64G01N21/78G01N27/48
CPCG01N21/33G01N21/6428G01N21/78G01N27/48
Inventor 郭佃顺吕晶黄丹丹赵梅张文馨周晓露
Owner SHANDONG NORMAL UNIV
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